US6031001A - Use of prostaglandins - Google Patents
Use of prostaglandins Download PDFInfo
- Publication number
- US6031001A US6031001A US08/809,017 US80901797A US6031001A US 6031001 A US6031001 A US 6031001A US 80901797 A US80901797 A US 80901797A US 6031001 A US6031001 A US 6031001A
- Authority
- US
- United States
- Prior art keywords
- prostaglandin
- derivative
- pgj
- composition comprises
- ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
- A61K31/5575—Eicosanoids, e.g. leukotrienes or prostaglandins having a cyclopentane, e.g. prostaglandin E2, prostaglandin F2-alpha
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Definitions
- Psoriasis is a common dermatologic disorder affecting 1-2% of the population e.g. in Europe and United States. The disease usually debuts between the age of 10-40 years, but may become manifest at any age. Typically hyperkeratotic pink lesions covered by adherent silver-white scales can be found in patients suffering from psoriasis. The lesions have a characteristic shape and are well-demarcated. Not infrequently these lesions are localised to the elbows, knees, the gluteal regions and the scalp and it is generally believed that a cause of the psoriatic lesions is physical contact, pressure e.g. rubbing.
- psoriasis The underlying mechanism of psoriasis is an increased proliferation of cells in the epidermis, primarily the keratinocytes. Thus, the epidermis becomes thick and hyperkeratotic, particularly superficially. The precise mechanism behind the stimulus of the cell proliferation is not known, but generally it is believed that trauma of the skin leads to an inflammatory reaction involving hyperproliferation of keratinocytes in the epidermis. There is a marked genetic disposition to develop psoriasis. Psoriasis may also become generalised over the whole body and psoriasis may cause arthritis, typically in the fingers. Psoriasis may fluctuate but complete and permanent remission is uncommon.
- Psoriasis is usually treated with different medications. In simple cases, keratolytics, lubricants and topical corticosteroids are employed. Salicylic acid and anthralin are also used.
- Another form of medical treatment is PUVA-treatment. PUVA-treatment is based on systemic or local administration of psoralens, e.g. methoxy-psoralen combined with irradiation of the skin with ultraviolet light (UVA). This treatment modality is effective but may predispose to skin cancer.
- Antimitotics, such as methotrexate have also been used in severe cases of psoriasis. Although there are presently many treatment modalities for psoriasis there is a definite need for more effective medications with less side-effects.
- Prostaglandins are fatty acids usually derived from the precursors eicosatrienoic, eicosatetraenoic or eicosapentanoic acid through metabolic steps involving oxygenation.
- Naturally occurring prostaglandins typically have the general structure ##STR1##
- the prostaglandins accordingly carry a cyclopentane ring to which two carbon chains link, the upper usually being called the alpha chain and the lower usually being called the omega chain.
- the prostaglandins are classified in subgroups A, B, C, D, E, F and J depending on the structure of the cyclopentane ring: ##STR2##
- the alpha chain is a 7 carbon carboxy-terminated aliphatic chain whereas the omega chain is a 8 carbon methyl-terminated aliphatic chain.
- subscripts of 1 to 3 are given.
- the double bond is situated between carbons 13 and 14 in the omega chain, and it exhibits trans configuration in naturally occurring prostaglandins.
- prostaglandins with subscript 2 e.g. PGA 2 and PGJ 2 an additional double bond in the cis configuration exists between carbons 5 and 6 in the alpha chain and finally in prostaglandins with subscript 3 a third double bond is situated between carbons 17 and 18 in the omega chain. This double bond also exhibits cis configuration in naturally occurring prostaglandins. All naturally occurring prostaglandins carry a hydroxyl group in carbon 15, which is essential for biologic activity.
- prostaglandins for treatment of a great number of various diseases, including psoriasis, has been suggested, especially in patent publications, but no efficient prostaglandin derivative has to be best of our knowledge been presented for treatment of psoriasis.
- Prostaglandins to be used according to the present invention are characterized by an ⁇ , ⁇ -unsaturated cyclopentenone and are in particular of the A and J type in which the cyclopentene ring has the basic structure. ##STR3##
- the prostaglandins that have been utilized in the exemplification of the present invention are PGA 2 and PGJ 2 .
- PGA 2 is probably not a naturally occurring prostaglandin in man, but it is formed from PGE2 during acid extraction.
- PGJ 2 on the other hand is a well known metabolite of PGD 2 , which is a naturally occurring prostaglandin.
- the molecular structures of PGA 2 and PGJ 2 are depicted in the figure given below. ##STR4##
- Prostaglandin A 2 ((5Z,13E,15S)-15-hydroxy-9-oxoprosta-5,10,13-trien-1-oic acid) and prostaglandin J 2 ((5Z,13E,15S)-15-hydroxy-11-oxoprosta-5,9,13-trien-1-oic acid) were purchased from Cayman Chemical Company (Ann Arbor, Mich., USA) and used in acid form. Both compounds were dissolved in ethanol, and diluted to the final concentration directly in the cell growth medium.
- Normal human epidermal keratinocytes (NHEK) derived from foreskin were purchased as secondary cultures (PromoCell, Heidelberg, Germany) and cultured in an optimized ready-to-use serum-free growth medium (KGM medium) (Promocell) at 37° C. in 5% CO 2 , humidified air.
- KGM medium serum-free growth medium
- the growth medium is a modification of the MCDB 153 formulation and is supplemented with various concentrations of human epidermal growth factor, insulin, hydrocortisone, bovine pituitary extract and gentamicin/amphotericin B (proportions proprietary information of Promocell).
- prostaglandins of the A and J type may be utilized for the treatment of psoriasis.
- two prostaglandins namely PGA 2 and PGJ 2 were used, but analogues and derivatives of prostaglandins of the A and J type with the same fundamental mechanism of action may also be employed.
- Analogues of PGA include e.g. 16,16-dimethyl-PGA 1 , ⁇ 7 -PGA 1 , ⁇ 7 -PGA 2 and 16,16-dimethyl-PGA 2 .
- Analogues or derivatives of PGJ include e.g. PGJ 1 , ⁇ 12 PGJ 1 and ⁇ 12 PGJ 2 .
- derivatives of the A and J type which are known from the literature and which are obvious candidates to be used for treatment according to the present invention.
- One such group is the derivatives containing a ring substituted omega chain disclosed in PCT application SE89/00475.
- alpha-chain modified prostaglandins may be employed, for instance derivatives containing alkyl substituents.
- PGA and PGJ or their analogues may be modified to more lipophilic substances by esterification of different parts of the molecule, e.g., the carboxylic acid moiety.
- esters that may be employed clinically because they penetrate better into the skin, comprise alkyl esters with 1-10 carbon atoms and especially short alkyl esters e.g. methyl, ethyl, and isopropyl or cyclic esters such as benzyl.
- the prostaglandin compounds and their esters or derivatives should be used in a suitable vehicle for topical application on the skin.
- a suitable vehicle includes aqueous vehicles with or without solubilizers, stabilizers such as cyclodextrins, oils, ointments, micelle systems, nanoparticles and various slow release formulations.
- Such vehicles may or may not contain preservatives depending on whether they are intended for single or multiple use.
- Various preservatives that may be employed comprise e.g. benzalkonium chloride, chlorhexidine, thiomersal, parabenzoic acid and other compounds with satisfactory antimicrobial effect.
- a formulation containing PGA 2 or PGJ 2 or derivatives of these prostaglandins is applied topically on the affected skin for different periods of time once or several times daily to treat the psoriatic lesions.
- Such treatment may take only a few weeks or may go on for longer times depending on the clinical situation.
- the recommended dose to be used depends on the particular prostaglandin and its physical-chemical characteristics but is usually in the range of from 0.01 to 100 ⁇ g per application. On an area of 1 dm 2 typically a dose of 0.1-10 ⁇ g per application is employed.
- the medication can be instilled once or several times daily depending on the clinical situation, and the dosage form.
- the psoriatic lesion has regressed treatment may continue intermittently or may be terminated.
- the invention also relates to the use of a a prostaglandin derivative as defined above for the preparation of a composition for treatment of psoriasis.
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
Claims (20)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9403158 | 1994-09-21 | ||
SE9403158A SE9403158D0 (en) | 1994-09-21 | 1994-09-21 | New use of prostaglandins |
PCT/SE1995/001059 WO1996009055A1 (en) | 1994-09-21 | 1995-09-19 | New use of prostaglandins |
Publications (1)
Publication Number | Publication Date |
---|---|
US6031001A true US6031001A (en) | 2000-02-29 |
Family
ID=20395309
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/809,017 Expired - Fee Related US6031001A (en) | 1994-09-21 | 1995-09-19 | Use of prostaglandins |
Country Status (10)
Country | Link |
---|---|
US (1) | US6031001A (en) |
EP (2) | EP1310256B1 (en) |
JP (1) | JP4044611B2 (en) |
AT (2) | ATE330613T1 (en) |
AU (1) | AU705901B2 (en) |
CA (1) | CA2200480C (en) |
DE (2) | DE69535081T2 (en) |
ES (2) | ES2194055T3 (en) |
SE (1) | SE9403158D0 (en) |
WO (1) | WO1996009055A1 (en) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020013294A1 (en) * | 2000-03-31 | 2002-01-31 | Delong Mitchell Anthony | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
US20020037914A1 (en) * | 2000-03-31 | 2002-03-28 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
US6476074B1 (en) * | 1997-07-10 | 2002-11-05 | Synphora Ab | Method and composition for treatment of erectile dysfunction |
US20040002514A1 (en) * | 2002-06-14 | 2004-01-01 | Alcon, Inc. | Topical use of hydroxyeicosatetraenoic acid compounds to treat psoriasis |
US6894175B1 (en) | 1999-08-04 | 2005-05-17 | The Procter & Gamble Company | 2-Decarboxy-2-phosphinico prostaglandin derivatives and methods for their preparation and use |
US20050159485A1 (en) * | 2002-01-04 | 2005-07-21 | Jost-Price Edward R. | Combinations for the treatment of immunoinflammatory disorders and proliferative skin diseases |
US20050222232A1 (en) * | 2000-03-31 | 2005-10-06 | Duke University | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
US20060041016A1 (en) * | 2004-08-17 | 2006-02-23 | Johan Stjernschantz | Composition and method for the treatment of psoriasis |
US20060100181A1 (en) * | 2002-05-03 | 2006-05-11 | Jost-Price Edward R | Combinations for the treatment of inflammatory skin disorders |
US20060121069A1 (en) * | 2000-03-31 | 2006-06-08 | Duke University | Compositions and methods for treating hair loss using oximyl and hydroxylamino prostaglandins |
US20100003289A1 (en) * | 2004-12-31 | 2010-01-07 | Hanmi Pharm, Co., Ltd. | Controlled Release Complex Formulation For Oral Administration of Medicine For Diabetes and Method For The Preparation Thereof |
US20100105775A1 (en) * | 2008-10-29 | 2010-04-29 | Delong Mitchell A | Amino acid salts of prostaglandins |
USRE43372E1 (en) | 1999-03-05 | 2012-05-08 | Duke University | C16 unsaturated FP-selective prostaglandins analogs |
US8722739B2 (en) | 2008-10-29 | 2014-05-13 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
US9328060B2 (en) | 2013-10-18 | 2016-05-03 | East Carolina University | J-series prostaglandin-ethanolamides as novel therapeutics |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5981586A (en) * | 1997-05-23 | 1999-11-09 | Pershadsingh; Harrihar A. | Methods for treating proliferative and inflammatory skin diseases |
FR2773075B1 (en) * | 1997-12-31 | 2000-05-05 | Cird Galderma | USE OF PPAR-GAMMA ACTIVATORS IN DERMATOLOGY |
SE9900672D0 (en) | 1999-02-25 | 1999-02-25 | Synphora Ab | Method and composition for prevention of scar formation in glaucoma filtration bleb and drainage fistula |
US7183316B2 (en) * | 2001-05-03 | 2007-02-27 | Cornell Research Foundation, Inc. | Treatment of HPV caused diseases |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4009282A (en) * | 1973-12-17 | 1977-02-22 | The Regents Of The University Of Michigan | Treatment of proliferating skin diseases with prostaglandins |
US4024174A (en) * | 1973-12-25 | 1977-05-17 | Ono Pharmaceutical Company | Tranes-delta 2-prostaglandins |
US4254145A (en) * | 1978-08-16 | 1981-03-03 | American Cyanamid Company | Topical application of prostaglandin hypotensive agents |
EP0097023A2 (en) * | 1982-06-10 | 1983-12-28 | Ono Pharmaceutical Co., Ltd. | Prostaglandin D derivatives, process for their preparation and compositions containing them |
EP0242580A2 (en) * | 1986-03-13 | 1987-10-28 | The Trustees Of Columbia University In The City Of New York | Use of A, B and C prostaglandins and derivatives thereof to treat ocular hypertension and glaucoma |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0569046B1 (en) * | 1988-09-06 | 2002-11-13 | Pharmacia Aktiebolag | Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
CZ277720B6 (en) * | 1990-12-29 | 1993-03-17 | Vysoka Skola Chem Tech | Pharmaceutic gel containing natural prostaglandins for topic use |
-
1994
- 1994-09-21 SE SE9403158A patent/SE9403158D0/en unknown
-
1995
- 1995-09-19 AT AT03000905T patent/ATE330613T1/en not_active IP Right Cessation
- 1995-09-19 AU AU35817/95A patent/AU705901B2/en not_active Ceased
- 1995-09-19 AT AT95933000T patent/ATE236638T1/en not_active IP Right Cessation
- 1995-09-19 ES ES95933000T patent/ES2194055T3/en not_active Expired - Lifetime
- 1995-09-19 CA CA002200480A patent/CA2200480C/en not_active Expired - Fee Related
- 1995-09-19 DE DE69535081T patent/DE69535081T2/en not_active Expired - Fee Related
- 1995-09-19 EP EP03000905A patent/EP1310256B1/en not_active Expired - Lifetime
- 1995-09-19 EP EP95933000A patent/EP0778774B1/en not_active Expired - Lifetime
- 1995-09-19 WO PCT/SE1995/001059 patent/WO1996009055A1/en active IP Right Grant
- 1995-09-19 US US08/809,017 patent/US6031001A/en not_active Expired - Fee Related
- 1995-09-19 ES ES03000905T patent/ES2263853T3/en not_active Expired - Lifetime
- 1995-09-19 DE DE69530303T patent/DE69530303T2/en not_active Expired - Fee Related
- 1995-09-19 JP JP51080696A patent/JP4044611B2/en not_active Expired - Fee Related
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4009282A (en) * | 1973-12-17 | 1977-02-22 | The Regents Of The University Of Michigan | Treatment of proliferating skin diseases with prostaglandins |
US4024174A (en) * | 1973-12-25 | 1977-05-17 | Ono Pharmaceutical Company | Tranes-delta 2-prostaglandins |
US4254145A (en) * | 1978-08-16 | 1981-03-03 | American Cyanamid Company | Topical application of prostaglandin hypotensive agents |
EP0097023A2 (en) * | 1982-06-10 | 1983-12-28 | Ono Pharmaceutical Co., Ltd. | Prostaglandin D derivatives, process for their preparation and compositions containing them |
EP0242580A2 (en) * | 1986-03-13 | 1987-10-28 | The Trustees Of Columbia University In The City Of New York | Use of A, B and C prostaglandins and derivatives thereof to treat ocular hypertension and glaucoma |
Non-Patent Citations (1)
Title |
---|
Chemical Abstract No. 121:91772j (Aug. 22, 1994). * |
Cited By (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6476074B1 (en) * | 1997-07-10 | 2002-11-05 | Synphora Ab | Method and composition for treatment of erectile dysfunction |
USRE43372E1 (en) | 1999-03-05 | 2012-05-08 | Duke University | C16 unsaturated FP-selective prostaglandins analogs |
US7074942B2 (en) | 1999-08-04 | 2006-07-11 | The Procter & Gamble Company | 2-decarboxy-2-phosphinico prostaglandin derivatives and methods for their preparation and use |
US7115659B2 (en) | 1999-08-04 | 2006-10-03 | The Procter & Gamble Company | Method of treating a condition by administering a prostaglandin derivative |
US6894175B1 (en) | 1999-08-04 | 2005-05-17 | The Procter & Gamble Company | 2-Decarboxy-2-phosphinico prostaglandin derivatives and methods for their preparation and use |
US20050124588A1 (en) * | 1999-08-04 | 2005-06-09 | The Procter & Gamble Comapany | 2-Decarboxy-2-phosphinico prostaglandin derivatives and methods for their preparation and use |
US20050124587A1 (en) * | 1999-08-04 | 2005-06-09 | The Procter & Gamble Company | 2-Decarboxy-2-phosphinico prostaglandin derivatives and methods for their preparation and use |
US8541466B2 (en) | 2000-03-31 | 2013-09-24 | Duke University | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
US20020037914A1 (en) * | 2000-03-31 | 2002-03-28 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
US9346837B2 (en) | 2000-03-31 | 2016-05-24 | Duke University | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
US9579270B2 (en) | 2000-03-31 | 2017-02-28 | Duke University | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
US20060121069A1 (en) * | 2000-03-31 | 2006-06-08 | Duke University | Compositions and methods for treating hair loss using oximyl and hydroxylamino prostaglandins |
US8618086B2 (en) | 2000-03-31 | 2013-12-31 | Duke University | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
US20020013294A1 (en) * | 2000-03-31 | 2002-01-31 | Delong Mitchell Anthony | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
US20060247214A1 (en) * | 2000-03-31 | 2006-11-02 | Duke University | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
US20070092466A1 (en) * | 2000-03-31 | 2007-04-26 | Duke University | Compositions and Methods for Treating Hair Loss Using C16-C20 Aromatic Tetrahydro Prostaglandins |
US20080241078A1 (en) * | 2000-03-31 | 2008-10-02 | Duke University | Compositions and methods for treating hair loss using c16-c20 aromatic tetrahydro prostaglandins |
US20090286769A1 (en) * | 2000-03-31 | 2009-11-19 | Duke University | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
US20050222232A1 (en) * | 2000-03-31 | 2005-10-06 | Duke University | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
US9675539B2 (en) | 2000-03-31 | 2017-06-13 | Duke University | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
US8906962B2 (en) | 2000-03-31 | 2014-12-09 | Duke University | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
US20050159485A1 (en) * | 2002-01-04 | 2005-07-21 | Jost-Price Edward R. | Combinations for the treatment of immunoinflammatory disorders and proliferative skin diseases |
US20060100181A1 (en) * | 2002-05-03 | 2006-05-11 | Jost-Price Edward R | Combinations for the treatment of inflammatory skin disorders |
US20040002514A1 (en) * | 2002-06-14 | 2004-01-01 | Alcon, Inc. | Topical use of hydroxyeicosatetraenoic acid compounds to treat psoriasis |
US20060041016A1 (en) * | 2004-08-17 | 2006-02-23 | Johan Stjernschantz | Composition and method for the treatment of psoriasis |
US20100003289A1 (en) * | 2004-12-31 | 2010-01-07 | Hanmi Pharm, Co., Ltd. | Controlled Release Complex Formulation For Oral Administration of Medicine For Diabetes and Method For The Preparation Thereof |
US8722739B2 (en) | 2008-10-29 | 2014-05-13 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
US8623918B2 (en) | 2008-10-29 | 2014-01-07 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
US20100105775A1 (en) * | 2008-10-29 | 2010-04-29 | Delong Mitchell A | Amino acid salts of prostaglandins |
US9328060B2 (en) | 2013-10-18 | 2016-05-03 | East Carolina University | J-series prostaglandin-ethanolamides as novel therapeutics |
Also Published As
Publication number | Publication date |
---|---|
DE69535081D1 (en) | 2006-08-03 |
EP0778774B1 (en) | 2003-04-09 |
JP4044611B2 (en) | 2008-02-06 |
EP1310256A3 (en) | 2003-06-25 |
ES2194055T3 (en) | 2003-11-16 |
ATE330613T1 (en) | 2006-07-15 |
CA2200480A1 (en) | 1996-03-28 |
AU3581795A (en) | 1996-04-09 |
AU705901B2 (en) | 1999-06-03 |
CA2200480C (en) | 2003-03-25 |
ES2263853T3 (en) | 2006-12-16 |
ATE236638T1 (en) | 2003-04-15 |
EP1310256A2 (en) | 2003-05-14 |
EP0778774A2 (en) | 1997-06-18 |
DE69535081T2 (en) | 2007-06-28 |
DE69530303T2 (en) | 2004-02-12 |
EP1310256B1 (en) | 2006-06-21 |
WO1996009055A1 (en) | 1996-03-28 |
SE9403158D0 (en) | 1994-09-21 |
JPH10505861A (en) | 1998-06-09 |
DE69530303D1 (en) | 2003-05-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US6031001A (en) | Use of prostaglandins | |
Kemény et al. | Dithranol: a review of the mechanism of action in the treatment of psoriasis vulgaris | |
US4839159A (en) | Topical L-carnitine composition | |
US5283257A (en) | Method of treating hyperproliferative vascular disease | |
US4871752A (en) | Use of aryloxycarboxylic acid derivatives against dermatological diseases | |
US5324746A (en) | Method of treating damaged mucosal and epithelial tissues with misoprostol | |
US6589990B1 (en) | Methods and compositions for misoprostol compound treatment of erectile dysfunction | |
FR2728790A1 (en) | COMPOSITION MODULATING APOPTOSIS COMPRISING METHONIAL OR ANY FACTOR INFLUENCING THE INTRACELLULAR METHONIAL RATE | |
US6380255B1 (en) | Treatment for dermal skin atrophy using thyroid hormone compounds or thyroid hormone-like compounds | |
CA2310049C (en) | Use of a mixture of a diol and an alpha-hydroxy acid for the treatment of hyperkeratotic skin diseases | |
US5254538A (en) | Method of treating periodontal disease | |
AU679818B2 (en) | Butyric ester cyto-differentiating agents | |
JPH04500824A (en) | Skin treatment methods to reverse the effects of photoaging | |
Ramamurthy et al. | Topically applied CMT-2 enhances wound healing in streptozotocin diabetic rat skin | |
EP0782447B1 (en) | Use of prostaglandins for the manufacture of a medicament for prevention and treatment of secondary cataract | |
EP0494995A1 (en) | Cosmetic method of inhibiting the formation of a scar | |
US5994399A (en) | Method of regenerating collagen-containing tissues with misoprostol | |
Oprica et al. | Overview of treatments for acne. | |
US20060041016A1 (en) | Composition and method for the treatment of psoriasis | |
US20060292185A1 (en) | Topical skin preparations for treatment of skin aging comprising a testosterone ester | |
OH et al. | M. GLOOR | |
MXPA00005078A (en) | Use of a mixture of a diol and an alpha-hydroxy acid for the treatment of hyperkeratotic skin diseases |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: PHARMACIA & UPJOHN AB, SWEDEN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:STJERNSCHANTZ, JOHAN;RESUL, BAHRAM;REEL/FRAME:008620/0877 Effective date: 19970430 |
|
AS | Assignment |
Owner name: SYNPHORA AB, SWEDEN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:PHARMACIA & UPJOHN AB;REEL/FRAME:009851/0717 Effective date: 19990305 |
|
CC | Certificate of correction | ||
FEPP | Fee payment procedure |
Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: SMALL ENTITY |
|
FPAY | Fee payment |
Year of fee payment: 4 |
|
FPAY | Fee payment |
Year of fee payment: 8 |
|
SULP | Surcharge for late payment |
Year of fee payment: 7 |
|
REMI | Maintenance fee reminder mailed | ||
LAPS | Lapse for failure to pay maintenance fees | ||
STCH | Information on status: patent discontinuation |
Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362 |
|
FP | Lapsed due to failure to pay maintenance fee |
Effective date: 20120229 |